HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-[2-(4-Cyanophenylethynyl)-6-methyl-8alpha-ergolinyl]-1,1-diethylurea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Ethynylbenzonitrile | HCID 4547245 | — |
| Reactant | 1,1-Diethyl-3-(2-iodo-6-methyl-8alpha-ergolinyl)urea | HCID 13559030 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-[2-(4-Cyanophenylethynyl)-6-methyl-8alpha-ergolinyl]-1,1-diethylurea | HCID 13822810 | 43.6% |
Reaction Steps
Under argon, 200 mg of 3-(2-iodo-6-methyl-8α-ergolinyl)-1,1-diethylurea is heated to 80°-90° C. in 4 ml of DMF with 4 ml of triethylamine, 4 mg of copper(I) iodide, 8 mg of palladium(O) tetrakis(triphenylphosphine) and 112 mg of 4-cyanophenylacetylene for 2 hours. After evaporation, the mixture is distributed in ethyl acetate and saturated sodium bicarbonate solution, and the organic phase is washed with saturated sodium chloride solution. After chromatography over silica gel with methylene chloride:ethanol=10:1, 87 mg of 3-[2-(4-cyanophenylethynyl)-6-methyl-8α-ergolinyl]-1,1-diethylurea is obtained, mp 150°-151° C., [α]D =+139.5° (c=0.2; pyridine).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04826851 |
| Source dataset | uspto-grants-1989_05 |
| ORD ID | ord-4602344eb51a40ec90c56811d3de7ba5 |
| Source note | uspto-grants-1989_05 |